Weston is a charming town located in Fairfield County, Connecticut, known for its serene natural landscapes, impressive architecture, and affluent community. The town offers a perfect balance between rural and urban living, making it a popular destination for those seeking a luxurious lifestyle.

Best choice of shopping

  1. The Weston Shops - a collection of boutique stores that offer a wide range of luxury items, including designer clothes, jewelry, and home decor.
  2. The Westport Country Playhouse - a cultural center that hosts various events throughout the year, including theater productions, concerts, and art exhibits.
  3. The Merritt Parkway - a scenic route that offers stunning views of the town's natural beauty and connects Weston to neighboring towns.
  4. The Shops at the Green - a shopping center that features a mix of high-end stores, gourmet restaurants, and specialty shops.
  5. The Weston Farmers Market - a weekly market that sells fresh produce, artisanal goods, and other locally sourced products.

Most luxurious hotels

  1. The Inn at Longshore - a boutique hotel that offers elegant guest rooms, an award-winning restaurant, and breathtaking views of the Long Island Sound.
  2. The Delamar Southport - a luxury hotel that features a spa, fine dining, and stylish accommodations.
  3. The Westport Inn - a historic hotel that combines old-world charm with modern amenities, including a fitness center, a pool, and a restaurant.
  4. The Westport Hotel - a chic and stylish hotel that offers comfortable accommodations, exceptional service, and an unbeatable location in the heart of downtown Weston.
  5. The Residence Inn Weston - a modern hotel that offers spacious suites, an indoor pool, and a complimentary breakfast.

For those looking for an excellent dining experience, Weston has a range of upscale restaurants that offer exquisite cuisine and a cozy atmosphere. Here are the 5 most luxurious restaurants in Weston:

  1. The Schoolhouse at Cannondale - a farm-to-table restaurant that serves innovative American cuisine using locally sourced ingredients.
  2. The Red Barn Restaurant - a classic New England-style restaurant that offers traditional dishes made with fresh, locally sourced ingredients.
  3. The Little Barn - a cozy gastropub that serves craft cocktails and delicious comfort food in a laid-back setting.
  4. The Gray Goose Cafe - a casual dining restaurant that offers a menu of classic American dishes, as well as vegetarian and gluten-free options.
  5. The Cottage - a charming restaurant that serves elevated New American cuisine in a rustic, romantic atmosphere.

World class Residences

  1. 25 Tannery Lane: This stunning estate sits on 6.31 acres and boasts over 13,000 square feet of living space. It features a grand two-story foyer, six en-suite bedrooms, an indoor pool, home theater, and a full gym.
  2. 23 Hidden Spring Road: This exceptional stone and shingle colonial is situated on 2.02 acres of beautifully landscaped property. The home features six bedrooms, a custom library, a home theater, and an outdoor pool with a waterfall.
  3. 20 Stonegate Lane: This magnificent stone and shingle colonial sits on 3.01 acres of meticulously landscaped property. The home boasts six bedrooms, a gourmet kitchen, a home theater, and a wine cellar.
  4. 60 Norfield Road: This stunning 1930s colonial has been completely renovated and features six bedrooms, a chef's kitchen, a home gym, and an outdoor pool with a spa.
  5. 5 Osborn Farm Road: This incredible home sits on over 4 acres of beautifully landscaped property and features six bedrooms, a grand two-story foyer, a custom home theater, and an outdoor pool with a waterfall.
Discover a stunning custom crafted luxury home, complete with a separate one bedroom guest pool house, that stands as an architecturally significant estate designed to be cherished.
$3,999,999
Courtesy of Redfin Corporation
This exquisite custom estate with pool site on 4.
$2,999,000
Courtesy of Coldwell Banker Realty
Come make 5 Woodland Way your new home !
$965,000
Courtesy of William Raveis Real Estate
Spacious 4 Bedroom Home on 2.
$1,149,000
Courtesy of Coldwell Banker Realty
Natural light, soaring ceilings, and a dramatic stone fireplace set the tone for this spacious contemporary on one of the best lots in a quiet cul de sac.
$1,374,000
Courtesy of William Pitt Sotheby's Int'l
This meticulous home was rebuilt and expanded in 2015, refinished floors and fresh paint in 2025, and is located on 2 sunny acres in lower Weston.
$1,495,000
Courtesy of Berkshire Hathaway NE Prop.
Discover exceptional living at this distinguished 5 bedroom, 3 bathroom ranch home spanning over 5, 000 square feet on prestigious Whippoorwill Lane in coveted Weston.
$1,139,000
Courtesy of Keller Williams Realty
A Timeless Sanctuary of Romance, Luxury, and Natural Beauty.
$1,995,530
Courtesy of William Raveis Real Estate
This charming 5 bedroom, 3 full bath home offers 2, 788 sq.
$920,000
Courtesy of O'Brien Premier Properties
Bringing the Indoors and Outdoors Together with Mid Century Rustic Elegance.
$1,160,000
Courtesy of Camelot Real Estate
Idyllic riverfront property in Lower Weston a builder's dream with both main house and barn transformations.
$1,050,000
Courtesy of William Raveis Real Estate
Welcome to this beautifully maintained 2 bedroom, 1.
$549,000
Courtesy of O'Brien Premier Properties
Storybook Charm Meets Modern Convenience in Lower Weston !
$675,000
Courtesy of Compass Connecticut, LLC
Welcome to your own private oasis at 30 Soundview Farm, sequestered on over 2 acres of breathtaking landscape ; a Michael Greenberg original.
$2,000,000
Courtesy of Higgins Group Real Estate
This modern farmhouse offers year round comfort and effortless entertaining !
$2,099,000
Courtesy of William Pitt Sotheby's Int'l
Tucked on a peaceful cul de sac in prime lower Weston, this contemporary gem is a rare find.
$1,700,000
Courtesy of Compass Connecticut, LLC
Discover the ideal site for your dream home with this exceptional 2.
$459,000
Courtesy of Compass Connecticut, LLC
Tranquil Contemporary Retreat on 2.
$820,000
Courtesy of Iron Gates Realty
Luxury Convenience Stunning Home Just Minutes from Merritt Parkway !
$1,599,000
Courtesy of William Pitt Sotheby's Int'l
80 K Price Reduction ! Amazing Value !
$899,000
Courtesy of William Raveis Real Estate
Experience dramatic, modern living in this grand home with a glorious gunite pool exceptional architectural appeal.
$1,779,000
Courtesy of Coldwell Banker Realty
Tucked away on a quiet cul de sac in sought after Lower Weston, this extraordinary 4 bedroom retreat redefines modern leisure living.
$1,650,000
Courtesy of William Raveis Real Estate
3 Mayflower Lane offers a perfect blend of modern sophistication and timeless charm.
$2,300,000
Courtesy of Compass Connecticut, LLC
This Charming 3 bedroom, 2 bath Colonial is ideally located close to downtown Weston !
$550,000
Courtesy of Redfin Corporation
New construction for SALE or RENT.
$1,499,000
Courtesy of Camelot Real Estate
27 acres of serene land along the Aspetuck River spreading between Weston and Fairfield.
$1,995,000
Courtesy of Keller Williams Realty
There are 21. 2 acres of undeveloped property, in the heart of Lower Weston in Fairfield County, waiting for you and the home s of your dreams or keep it ...
$429,900
Courtesy of RE/MAX Heritage
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